


Late Night

by SPNfan121



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Boss/Emloyee Sex, Bottom Sam wesson, Caught watching porn, Dirty Talk, First Kiss, First Time, Hand Jobs, M/M, Masturbation, Office Sex, Porn Watching, Top Dean Smith
Language: English
Status: Completed
Published: 2018-12-14
Updated: 2018-12-14
Packaged: 2019-09-18 05:12:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,371
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16988658
Author URL: https://archiveofourown.org/users/SPNfan121/pseuds/SPNfan121
Summary: Dean is working late at the office. Because he’s bored, he just decides to watch some porn in his office. When Sam comes back to his office, things started to get interesting.





	Late Night

**Author's Note:**

> I hope you are enjoying my story and have fun reading it.

Dean's still sitting in his office and looks into his computer. He can't concentrate on his work, he just wants to go home, maybe eat something and then go to bed. Sometimes he wishes that he wasn't the boss, rather a simple employee. So he just could go home around the afternoon and hasn't to sit here in the evening to finish his work.

Dean sighs and leans back in his chair. How much he wants to get this work done, he just can't concentrate and he didn’t want to try it anymore.

He pushed his worksheets aside and opened the internet. He typed into the browser a porn side and clicked at the first result that showed up. A big smile appeared on his lips. He was glad that at his computer the internet behavior wasn’t controlled as much as with his employees. One thing he actually loved about being that boss. 

No one knows that he's watching porn on his office computer. But at nights like this, he just couldn't resist. It was the perfect timing, so why should he not use these? 

After the porn side opened up, he searched for gay porn and licked his lips as he saw the result to this. He scrolls through the first page. But it seems like nothing could gain his attention. 

He clicks through the pages and hops that something could catch his eyes. After a few seconds of searching, he found an interesting title. Boss fucks employee in his office on his desk. Fuck, he feels how his cock is getting hard and he hasn't even clicked on the video.

Dean clicks on the video and increased the volume. 

At the beginning of the video, Dean saw a tall man in a suit sitting on his desk and does his work. Then Dean hears a knock on the door and a man slowly entered the room. 

“You wanted to see me?” asked the employee. 

“Yes, I need to talk to you,” answered the boss and stand up from his desk and walks towards the other man. 

“Yes.”

“I must confess that I have not been so happy with your work lately. Apparently, you lack the motivation. I think we should change that as soon as possible. Is there anything that could raise your motivation?"

“I don’t you,” said the employee and looked down. 

The boss in the video moves a little closer to his employee, so he was now in his personal space and raised that chin with his middle and index finger.

“When was the last time you had sex?” asked the boss in his deep voice. 

Dean could feel his cock twitching in his dress pants. He opens the button and pulls the zipper down before he lifts his hips and pulls the pants down to his knees. In a quick movement, he frees his cock from his boxer briefs and strokes his cock lazy.

“That was a while ago,” admit the employee and just wants to look away again but his boss stopped him from doing that. 

"I think we can change that," said the boss and starts to undress his employee's dark blue blazer, before he went on opening the buttons of his shirt. 

The employee licks his lips and moans softly as his boss brushed his shirt over his shoulders and it fell to the ground. 

A second later, the boss opens the pants from the other man and pulls them down with his boxer briefs. 

Dean couldn’t hold back the moan as he saw the big cock from that man. It was beautiful and hard and on the tip could he see the first drops of pre-come. Fuck, he could also feel how he was leaking pre-come himself. 

The employee gets the request to undress his boss. A second later the employee undressed his boss, while his boss was kissing him hard and a low moan from the computer was filling Dean’s office. 

Dean licked his lips, enjoying the moan of the man and strokes his cock a little harder. Fuck that feels good. 

The boss broke away from the kiss and moves his hands to the other man's shoulders to get him on his knees. With lust in his eyes, the employee stares up to his boss, while opened his pants and briefs down, revealed his boss’ cock. 

Again, Dean couldn’t hold back the moan and he doesn’t want to either. That cock was a little thicker than from the other man and he just wished he could climb into the computer and sucks that big cock until that guy was coming down his throat. Just the thought of it makes his cock leaking even more pre-come than before. 

The employee puts his hand around his boss’s cock and strokes it gently. His boss moans and throws his head back and his hips jerk towards. 

Dean feels how his lips escape a moan as he plays with the tip a little, rubbing the pre-come around his cockhead. 

He couldn’t tear his eyes away from the screen as the employee puts his lips around the cock of his boss and sucks on it. 

“Fuck, I want someone to suck my cock,” said Dean and strokes his inner thigh. 

He hears the moan from the taller guy and suddenly Dean has to think of his employee. Sam Wesson. That guy was tall and Dean bets that his cock was not so small either. What would he give to have Sam Wesson on his knees in front of him, sucking his cock? That would be that hottest sex in his whole life and the fact he was his boss would it makes it even hotter.

A little too hard, Dean saw how the boss pushed his employee away and with a loud pop the employee release the cock from his mouth. Then the employee stands up and the boss grips his arm turned him around and pushed him against the desk, the boss was behind him. 

“Now things start getting interesting.” Dean has a big smirk on his face as the video went on and the boss grips the employee’s hips with one hand well the other get a hold on his cock, stroking it a little bit. 

With one movement he was inside the employee and he moans deep. Dean knows that this part was always fake because never would a guy without a warm-up put his cock inside another guy. In real life, it would hurt so bad and maybe after that, you need to go to the hospital and Dean doesn't want to have this experience. Ever. 

The boss was poking inside the employee and Dean keeps stroking his cock; before he moves down to give his balls a little squeeze. 

Dean was so lost in his own pleasure that he doesn't notice that someone entered the room.

"So this is what you are doing when you're alone," said a familiar voice and Dean almost fells of his office chair. Sam was standing in front of his desk and had a smile on this face. 

“Ahm… I was… ahm…” Dean doesn’t know what to say or do. This was so embarrassing right now and he wished that the ground opened so that he could disappear into it.

A few seconds where silence inside the room, besides the fake moans from Dean’s computer. Dean turns off the volume and looked at his employee with red cheeks. 

“What are you doing here, anyway?” asked Dean when he found his voice again.

“I just wanted to pick up my cell phone. My sister called me on the house phone tonight and said she had tried it on my cell phone 20 times and I didn’t answer it. Only then did I notice that I don’t have my cell phone with me.”

"And then you thought that you just go to the office again and get it?" Dean raised an eyebrow.

“Yes,” said Sam. Like it was the most normal thing in the world. Maybe for Sam, it was.

“Okay.” 

Dean bites his lip. What should he do now? It was still embarrassing and he was still hard. This whole thing was so fucked up. 

"So what are we doing now?" Dean was surprised that he could still keep eye contact, even when his cheeks were a little red.

“I don’t know. What were you about to do?” Sam asks and walks towards his boss and has still a big smile on his face. 

“Why are you smiling?” Dean was a little confused. 

“Because I was never dreaming that I would catch my boss watching gay porn on his office computer and I found it really funny.” Sam’s voice was calm and he laughs a little. 

Dean broke the eye contact and turns the internet off before he was looking at Sam again.

“It’s really embarrassing,” admit Dean and looked down just to realize that his cock was still hard and lying against his shirt now, leaving pre-come there. 

“Did you think of someone when you watched that porn?” Sam was curious now. Did Dean think of someone, while he was watching porn? 

“Yes.”

“Who did you think of?” 

“You.” 

Just one word and Sam feels like he’s gone passed out or would forget to breathe. Dean was thinking of him? Could it be that Dean was gay? Maybe when he was watching gay porn but could it also be that Dean was interested in him? 

After the first shock, Sam decides to walk a little closer to his boss, now he was standing in front of him, looking down, because he was taller. 

“So you want me to do what?” asked Sam and sounds very seductive. His voice was deep and he could see how Dean’s cock twitched a little. Sam couldn’t hide his smirk. 

Dean just sits in his chair and looked up at Sam, who was very tall, but to be honest he liked tall man especially when it comes to sex. And his fucking voice, had Sam ever sounded so sexy because Dean has never ever in his life heard such a deep voice. He could feel how his cock twitched a little and he just wants Sam to get on his knees and sucked his cock. He wants to feel this pretty mouth around him.

“There are so many things I want you to do to me,” answered Dean and licked his lips. 

"So then tell me about your fantasies?" Sam was so excited to hear all this dirty thought from his boss.

“First I want to feel your big hand around my cock, starting with a good handjob and then I want you to suck my cock into your mouth. I want to feel those pretty lips around my cock."

“Sounds good to me, but can I kiss you first, because I was fantasizing about you too and I want to feel those beautiful lips on my own.”

“So you’re gay?” 

“Yes.”

Dean couldn’t believe how lucky he was. His employee was gay. The night starts to get better and better. 

He stands up from his chair and pulls Sam closer, reaching his hand out to stroke his cheek and was not surprised to feel soft and warm skin there. 

Automatically, Sam closed his eyes and leans into the touch. Those rough fingers felt really amazing on his skin and he knows he couldn’t get enough and wants to feel these fingers somewhere else. 

Gently, Dean pulls Sam face towards him and locked his lips with Sam’s. Sam’s lips were so warm and soft, like his skin. Dean escapes a sigh. Slowly their lips moved against each other. 

The kiss was tender and slow, they wanted to get used to that feeling they felt right now. 

Sam could feel how the passion starts to grow in his crotch and how his cock slowly shows interest in this situation. 

With every second the kiss gets more and more passionate. Sam grips Dean’s hips and pulls him closer, while his tongue slides into Dean’s mouth. Their tongues played around each other. 

Both of them groaned into the kiss before Dean pulls away after a few seconds. They're both tried to catch their breath, while they were looking at each other.

“You’re a good kisser,” said Sam and moves his hands under Dean’s shirt and feels warm skin. 

“I could say the same thing about you,” replied Dean and closed his eyes, enjoying the feeling of Sam’s hands on his skin. 

Slowly, Sam pushed Dean backward, because his pants were still opened and a second or two later Dean was sitting in his chair again. 

"So I think I'll make your dreams come true, don't you think?” asked Sam as he was opening his pants and pulls them down as well as his boxer briefs and frees his hard cock. He takes off his shoes and pushed his clothes aside. 

Dean’s mouth starts to water, as he sees that beautiful cock for the first time and for sure everything on Sam’s body was a little bigger than others. 

“Maybe I let you suck my big cock as well,” said Sam with an evil grin on his face, like he was reading Dean’s mind. 

“That would be really awesome”, said Dean and in his mind, he imagined what it would be like to feel that cock inside his mouth.

Sam went on his knees and grips Dean’s cock with a firm grip. Slowly moves his hand up and down and listen to his boss moans. How many times had he image what Dean would sound like during sex and after hearing the first moans he couldn’t get enough of it. 

“Oh yes, that feels good,” moaned Dean and throws his head back, closing his eyes. Dean moves his hand into Sam’s hair and stokes it. He can’t wait to feel Sam’s mouth. 

Sam doesn’t have to ask if his boss likes it, because Dean’s moans say a lot. Sam moves his thumb over Dean’s slit, rubbing the pre-come over Dean’s cockhead and teasing him a little. 

“Fuck, can you put your mouth around me and suck me, please,” Dean begs and opened his eyes slowly, looking down just to see that Sam smiles up at him. 

“Just because you asked so nicely,” said Sam and does exactly what Dean was asking for. 

The first second Sam has his lips around his cock, Dean was afraid to come right away. Fuck, do Sam’s lips feel so good. Dean grips Sam’s hair a little rougher than before and pulls him closer to his crotch. He wants more, much more. 

Sam doesn’t seem to mind, while he was sucking his boss’s cock into his mouth. He tastes the salt and bittersweet taste of Dean’s pre-come, which makes him moan a little around the cock. He has never thought that someday he would be on his knees in his boss’s office and suck his cock. 

“Fuck, Sam. You’re so good at this,” moaned Dean and looked down at his employee, who was sucking at his tip. 

Sam moans responds and begins to suck a little harder. He loves the feeling of Dean’s cock inside his mouth, loves the feeling of the pre-come on his tongue. 

Suddenly, Sam gets pushed away from Dean's cock and looks up at him in confusion.

“I don’t want to come like this. I want to fuck you,” explained Dean his behavior. He takes off his shoes and pulls his pants and boxer briefs from his body before he stands up and opens the drawer to grip the bottle of lube, which was lying in there and a condom. 

Sam could feel how his cock was getting even harder at Dean’s words. Slowly he stands up and looked at his boss. 

Dean walks around his desk and Sam followed him. 

“Lean against the desk,” ordered Dean and Sam does what he was told to do. 

“I’m going to suck your big cock first and then I’ll fuck you.” Dean continues and went on his knees, looks up at Sam, while he was gripping his cock and slowly moves his hand up and down. 

A low moan escapes Sam’s lips, as he felt the strong hand on his cock. Dean knows exactly what feels good and teased the tip of Sam’s cock with his thumb. 

“Fuck, Dean,” Sam hisses and throws his head back in his neck, his eyes closed. His boss really knows what feels good. 

"You like this, Sammy?" asked Dean and grips Sam's balls just to give them a gentle squeeze.

“Yes, please, don’t stop,” begged Sam and looked down at his boss. Dean looked so fucking beautiful on his knees. What it would feel like to have these beautiful soft lips around his cock? He couldn’t wait to find out. 

“Now I’m going to suck you,” told Dean Sam and puts his lips around the cockhead. 

The first touch of Dean’s lips around Sam’s cock was amazing. And Sam was afraid to come just from that. Automatically, Sam moves his hand into Dean’s short hair and grips it tightly. He needs something to hold onto. 

“Dean, you’re so good. Your lips were really made for sucking cock," moaned Sam and moves his hips, thrust a little into Dean's mouth. Not too much because Sam doesn’t want Dean to choke on his big cock. 

Dean couldn’t help himself to moan a little around Sam’s cock either. Sam’s cock was so fucking beautiful. He was big and thick and just amazing. He moves his head back and teased the tip with his tongue, tastes the pre-come and moaned again. His employee tasted really good. Before he moves his head back down Sam’s cock, squeeze Sam’s balls with his hand gently and gets another moan from Sam. 

But Dean doesn’t want Sam to come like this. He wants to fuck Sam so hard, so he wouldn’t be able to sit on his fucking chair for a week. Yes, he wants that. He wants Sam to remind who fucked him that good. 

Dean pulls away from Sam’s cock and stands up, smiling evilly, as he was looking into Sam’s eyes. Sam doesn’t know what to think and he wasn’t sure if he really wants to know that. 

“I’m gonna fuck you so good and hard. You wouldn’t be able to sit for a week,” told Dean his evil plan. 

“Let’s see how good you are. Or if these are just empty promises, huh?”

“So you want to challenge me? You will already see what you have from it?” Dean was so ready to take on this challenge. 

“Turn around and show me that sweet ass of yours,” ordered Dean and Sam does what he was told. 

Sam leans against the desk with his ass up in the air in front of his boss. And shit, his cock was getting harder than before. 

Dean grips both cheeks with a firm grip and pulls those cheeks apart to get a look at this sweet tight hole of Sam. 

And god, Sam’s hole looked so fucking tight. What it would be like to get his cock inside there? He reaches for the bottle of lube on the desk and opened it. Than Dean presses a small amount onto his fingers and put the bottle on the desk again. 

He’s warming the gel up with his fingers before he moves his finger between Sam’s cheeks, circling around Sam’s hole. 

Sam gasped in surprise, his eyes wide open. It wasn't his first time with a man, sure but his last time with a man was a few months ago, so he needed to get used to that feeling again.

“You’re okay?” asked Dean gently. He doesn’t want to hurt Sam. 

“Yeah, I’m okay. It’s been a while since my last time, that’s all”, answered Sam and looked over his shoulder to his boss. 

“I’ll be careful. I promise.” Dean smiles at Sam and puts his left hand onto Sam’s hips to keep him steady. 

Sam turned his head again and was looking at the wall in front of him. 

Carefully, Dean pushed his finger inside Sam. Give his employee enough time to get used to the feeling. Slowly he moves his finger inside Sam. And shit, Sam was tight and hot inside. Dean couldn’t wait to put his fucking dick inside that heat. 

Sam moans in pleasure, closing his eyes and holds onto the desk in front of him. Fuck, he almost forgot how good that feels. He couldn’t help himself and moves his hips into Dean’s direction. He doesn’t care how slutty that was but he wanted more.

“Fuck, that feels good,” moaned Sam. And it was just Dean’s finger. How would it feel like to have his cock inside him? 

Dean licks his lips as he saw this. Sam was already a fucking slut for his cock and he loves it. 

“You’re a little slut, aren’t you? I only have one fucking finger inside you and you already begging for more am I right?” 

“Yes, oh god, yes. Please, give me more,” moaned Sam and he could hear Dean’s laugh behind him. 

“You are a slut for my cock but don’t worry baby, I’m gonna fuck you soon.”

A few times Dean moves his finger in and out before he adds a second finger. 

Sam moans in response and he feels how he was starting to sweat.

Dean moves his fingers inside Sam going a little deeper with every second until he was hitting Sam's prostate.

Sam almost screamed at the pleasure which was taking over his whole body. 

“You’re lucky that we’re alone because by now everyone would know that we’re having sex in my fucking office,” said Dean and pushed his fingers deep into Sam. 

“Stop talking and do that again, please,” begged Sam and spread his legs a little wider for Dean. 

Dean growls in response. Holy shit, Sam was really a slut for him and he really liked that.

“You’re really a slut, huh?” asked Dean but did what Sam has told him to do, hitting Sam’s sweet spot every time he drives his fingers back inside Sam. 

“Yeah, right there, oh god, that feels so good.” Sam just moans and moves his hips, while Dean was fucking him with his fingers. 

Dean adds a third finger and scissors his finger to get Sam finally ready for his cock. Dean wants that so bad he couldn’t hold it back any longer. His cock was so hard that he thought he was about to die if he didn’t get any salvation soon. He removes his finger and hears a frustrated noise coming out of Sam’s mouth. 

Suddenly Sam feels so empty and he doesn’t like that feeling but he also knew that Dean’s about to put his cock inside him and he was so excited. 

Dean gets a hold on his cock and slowly teased the rim with his tip, leaving his pre-come there. 

“Please, Dean. Stop teasing and just do it.” Sam sounds desperate and he wants to feel Dean’s cock inside him. 

“Just a second”, said Dean and grips after the condom, which was still lying on the desk and opened it and put it out before he rolls it over his hard cock. 

After that was done he pressed his cock against Sam’s rim, just a little without entering. 

“That’s so not fair, Dean. Fuck, please, just fuck me already.” Sam sounds so desperate. He wants to get fuck. 

“After you asked so nicely, I’ll do what you want,” said Dean and pushed finally his cockhead into Sam’s tight ass. 

Sam groans and throws his head back, feeling nothing but the stretch of Dean’s cock inside him. 

Dean needs to control his breathing because he was afraid to come right now. Sam was so fucking tight and hot around his cock. It felt amazing. He slowly starts to move and get Sam used to that feeling of having him inside him. 

Sam moans softly with the careful movements of Dean’s cock inside of him. 

“You like that, don’t you? Having my cock inside that tight ass of yours, hm?” asked Dean and strokes Sam’s hips of every thrust. 

“Yeah, you feel so amazing.” Sam moans between his words and Dean loves that, that’s for sure. 

"I bet I do," answered Dean and thrust a little deeper inside Sam to hit his prostate with every thrust.

Sam moans and gasps as he moves his hips to meet Dean’s thrust. Fuck that feels really good and he gets a hold of his cock. 

“It’s okay, Sammy. Touch yourself,” ordered Dean and moves his hips faster to fuck him a little harder. 

Sam strokes his hard cock in the pace Dean was pushing inside him. 

Sam could feel how his orgasm builds inside of him. His balls were heavy and full and he was a few seconds away from coming in his hand. He teased the slit a little and that was it. Sam comes with Dean’s name on his lips and was shaking a little as his orgasm rushed through him. His hand and also the desk was covered in his come.

Dean feels like his cock was in a vice because Sam getting even tighter now after he comes. Dean thrust once or twice inside Sam's hole before he was coming as well inside his condom and screamed his pleasure out. 

Nothing was heard in the room besides their heavy breathes. 

Gently, Dean puts his cock out and removes the condom, made a knot before he was throwing it into the trashcan, which was under his desk. 

“Fuck that was hot and intense,” said Sam, still breathless. 

“Yeah, it was,” agreed Dean and has a satisfying smile on his face. He turns around to face Sam again, reached out for him and pulls him into a gentle kiss. 

“Maybe we should get dressed and go home,” said Dean and pulls away from Sam. 

Sam nods and both of them walk around Dean's desk to grab their clothes and get dressed.

After that Dean turns off his computer and both were leaving his office.


End file.
